South Shore Fall Festival Preview

From Oktoberfests and harvest time fun to spooky Halloween trails and brew and wine fests, here's a look at what fall events you can expect in Northwest Indiana all season long! 

September 2025 Festivals

September starts with a bang this year, with three of the largest festivals of the season coming on September 6th. Empanada Fest at Whiting Lakefront Park features plenty of food, live music, entertainment and a beer garden. Come celebrate and welcome the monarch butterflies as they cross through Indiana with the Festival de la Monarca at Kosciuszko Park in East Chicago with arts and crafts, music and food. At the Valparaiso Popcorn Festival, which started in 1979, visitors can watch the Popcorn Parade and enjoy the Poppin' Play Zone, beer garden, music and tons of vendors in downtown Valpo.

September 13th is a great day for wine lovers! Sample fine wines, grab a bite and listen to live music at Vino Al Fresco at Thomas Centennial Park in Chesterton and the Crown Point Wine Fest at Bulldog Park in Crown Point. There's also Rock the Arts at Carpenter Creek Cellars in Remington, blending fine arts, live music and maybe a glass or two of wine. The full weekend, September 13-14, celebrates the fall harvest! At Fair Oaks Farms' Applefest, you can pick apples and enjoy some sweet apple treats. 

For the creative ones, Art Blitz on September 20th at Art Barn School of Art in Valparaiso is an interactive exploration of the arts with activities, exhibits, artist demos, hayrides and music. Or if you're ready to ease into the Halloween season, Haunted Hills Haunted Attractions has Fall Festival on September 27th. Activities include a gel blaster arena, photo ops, escape rooms, carnival games, face painting, magic shows and more.

Finish off September by finishing off a few samples of craft beer at Valpo Brewfest on September 27th in Central Park Plaza. Or at Oktoberfest from September 27-28, where Fair Oaks Farms will be pouring some fall brews along with German fare and games for every age, like stein holding and the soybean maze!

October 2025 Festivals

If you're looking for another German fest, Crown Point is hosting its Oktoberfest at Bulldog Park on October 4th with a beer garden, food, hayrides, a bean bag tournament and more. If you'd rather skip right ahead to frightful fun, Wickedly Whiting is October 3-4 in downtown Whiting with spooky vendors, mystifying entertainment and activities for all. Munster is getting into the Halloween spirit, too, with Pumpkins, Witches and Hayrides, Oh My! at Centennial Park on October 4th, where kids can visit the pumpkin patch, meet some characters, go on a candy hunt, ride a pony and more.

For oversized fall entertainment, Fair Oaks Farms is hosting Pumpkinfest October 11-12, with giant pumpkins, snacks, signature drinks and all kinds of pumpkin-related activities like pumpkin bowling, ring toss or head balance. Later in the month, on October 25th, Fair Oaks brings in a host of characters to hand out candy along the Halloween Trail, which is included in your orchard admission, so you can pick some pumpkins and apples while you're there, too! 

For more Halloween entertainment, Friendship Botanic Gardens in Michigan City has Haunted Trails on October 26th. Wear your costumes for an afternoon of exploring the gardens, games, cider, crafts and stories. And don't forget Haunted Hills Haunted Attractions' creepy park comes to life all month, with another family-friendly Fall Festival on October 18th.

November 2025 Festivals

Rounding out the fall and bringing in winter are these fun November events. November 1st brings in the Pumpkin Smash Bash at Fair Oaks Farms, where visitors can smash a section of pumpkins to fertilize the land for next year's batch. The Festival of Owls is on November 15th at the Porter County Expo Center in Valparaiso. Meet and greet live owls, shop local vendors and enjoy plenty of educational activities for kids.

Finally, the Gobble Gobble Thanksgiving Turkey Walk at the Friendship Botanic Gardens in Michigan City on November 27th allows kids and adults alike to hike through the garden trails, looking for hidden turkeys that can be redeemed for a prize.